Stereochemistry | RACEMIC |
Molecular Formula | C11H17NO |
Molecular Weight | 179.2588 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CNC(C)CC1=CC=C(OC)C=C1
InChI
InChIKey=UGFMBZYKVQSQFX-UHFFFAOYSA-N
InChI=1S/C11H17NO/c1-9(12-2)8-10-4-6-11(13-3)7-5-10/h4-7,9,12H,8H2,1-3H3
Molecular Formula | C11H17NO |
Molecular Weight | 179.2588 |
Charge | 0 |
Count |
MOL RATIO
1 MOL RATIO (average) |
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
4-Methoxymethamphetamine (PMMA, para-Methoxymethamphetamine) is a stimulant and psychedelic drug closely related to the amphetamine-class serotonergic drug para-methoxyamphetamine (PMA). Little is known about the pharmacological properties, metabolism, and toxicity of 4-Methoxymethamphetamine. Because of its structural similarity to para-methoxyamphetamine, which has known toxicity in humans, it is thought to have considerable potential to cause harmful side effects or death in overdose. In the early 2010s, a number of deaths in users of the drug MDMA were linked to misrepresented tablets and capsules of 4-Methoxymethamphetamine. In 2010–2013, a cluster of 29 fatal poisonings related to the toxic designer drug 4-Methoxymethamphetamine was revealed in Norway. The toxicity of PMMA is regarded as substantially higher than for amphetamine, methamphetamine, and MDMA, as indicated by 131 fatal and 31 nonfatal poisonings associated with the abuse of 4-Methoxymethamphetamine worldwide. The toxicity of 4-Methoxymethamphetamine is positively correlated with the 4-Methoxymethamphetamine dose and the blood drug level, but the existing literature indicates that certain human subjects may have an increased risk of 4-Methoxymethamphetamine toxicity. 4-Methoxymethamphetamine, like PMA most likely acts as a selective serotonin releasing agent (SSRA) with weak effects on dopamine and norepinephrine transporters. However, relative to MDMA, it is considerably less effective as a serotonin releaser with properties more akin to a reuptake inhibitor in comparison. It evokes robust hyperthermia while producing only modest hyperactivity and serotonergic neurotoxicity, substantially lower than that caused by MDMA.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
83.0 µM [IC50] | |||
7.4 µM [IC50] | |||
180.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
PubMed
Patents
Sample Use Guides
Human embryonic kidney (HEK) 293 cells stably expressing human DAT, NET or SERT were used for activity evaluation. Uptake activity of hNET, hDAT and hSERT was measured using the
Neurotransmitter Transporter Uptake Assay Kit from MDS Analytical Technologies (Sunnyvale, CA). On day 0, HEK 293 cells were seeded at a density of approximately 60.000 cells/well in clear-bottom, black-walled, 96-well plates (Greiner Bio-one, Solingen Germany) coated with PLL buffer (50 mg/L). Cells were allowed to proliferate overnight in a humidified 5% CO2/95% air
atmosphere at 37 °C. Experiments were performed the next day (day 1). Cells were pre-incubated with the fluorescent substrate for 12 min prior to a 30 min drug exposure. Culture medium was replaced by 100 μL/well fluorescent substrate solution, and uptake measurements were started. At t= 0, 100 μL/well HBSS without (control) or with drug was added to each well and uptake was measured continuously for 30 min. Background wells were pre-incubated with 100 μL/well HBSS without fluorescent substrate solution and exposed at t =0 min to 100 μL/well HBSS without drugs. Non-transfected HEK 293 cells pre-incubated with 100 μL/well fluorescent substrate solution and exposed at t= 0 to 100 μL/well HBSS without drugs served as negative controls. Drugs were prepared daily in HBSS from 2 or 100 mM stock solutions. Cocaine, DL-amphetamine, MDMA, 4-FA, MXE, PMMA, 2C-B, 25B-NBOMe, 25I-NBOMe, α-PVP and 5-APB were measured at final concentrations of 0.01–1000 μM.